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Variations in the intermolecular interactions in (E) benzaldehyde 7-chloro-1-methyl- 4H-quinolinyl-4-ylidene-hydrazone and seven halo derivatives

  • Marcelle de L.F. Bispo , Camila C. de Alcantara , Solange M.S.V. Wardell , Marcus V.N. de Souza and James L. Wardell EMAIL logo
Published/Copyright: March 1, 2016
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Zeitschrift für Kristallographie - Crystalline Materials
From the journal Zeitschrift für Kristallographie - Crystalline Materials Volume 231 Issue 4

Abstract

Eight crystal structures are reported here: substituted (E) benzaldehyde 7-chloro-1-methyl-4H-quinolinyl-4-ylidene-hydrazones, 1, [substituted benzaldehyde: XYC6H4CHO: X,Y=H,H; 2-F,H; 3-F,H; 4-F,H; 3-Cl,H; 4-Cl,H; 2-Br,H and 2,3-Cl2]. None of the molecules, 1, are overall planar: angles between the phenyl and and quinolinyl rings vary from <5°, for (1:X,Y=3-F,H; 4-F,H; 3-Cl,H and 2,3-Cl2) to 15–16° for (1: X,Y=H,H and 4-Cl,H). The supramolecular arrangements in the parent compound (1: X=Y=H) are generated solely from C–Z···π (Z=H and Cl) interactions, while the supramolecular arrangements for each of the halo derivatives arise from combinations of π···π and some of C–Z···π (Z=H, F, Cl) and C–H···Z (Z=N, F, Cl) intermolecular interactions: in each case different assemblies result. While there are possibilities for π(quin)···π(quin), π(quin)···π(phen) and π(phen)···π(phen) interactions [quin and phen refer to the quinolinyl and phenyl moieties], only compounds (1: X,Y=2,3-Cl2) and (1: X,Y=4-Cl,H) exhibit all three, (1: X,Y=2-Br,H) just π(quin)···π(quin) of the three, and in the others two of the three. All the halo derivatives exhibit π(quin)···π(quin) interactions. It is argued that steric hindrance between molecules, generated by the halo substituents, prevents the halo derivatives from adopting the packing arrangements of the parent compound, (1: X,Y=H,H). As there appears to be no reason, steric or otherwise, why compound (1: X,Y=H,H) cannot utiilize π···π interactions, it is apparent that the packing of molecules via the C–Y···π interactions is the most stable.

Keywords: crystal structures; hydrazones; quinoline derivatives; π···π stacking interactions

Acknowledgments

The use of the NCS crystallographic service at Southampton and the valuable assistance of the staff there are gratefully acknowledged. JLW thanks FAPERJ and CNPq, Brazil for support.

References

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Supplemental Material:

The online version of this article (DOI: 10.1515/zkri-2015-1893) offers supplementary material, available to authorized users.

Received: 2015-8-27
Accepted: 2015-11-28
Published Online: 2016-3-1
Published in Print: 2016-4-1

©2016 by De Gruyter

Articles in the same Issue

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  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Single-crystal X-ray diffraction study of Cs2Er[Si6O14]F and Cs2Er[Si4O10]F
  5. Rb2Ca2Si3O9: the first rubidium calcium silicate
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  7. Variations in the intermolecular interactions in (E) benzaldehyde 7-chloro-1-methyl- 4H-quinolinyl-4-ylidene-hydrazone and seven halo derivatives
  8. Crystal structures of 3-(2H-1,3-benzodioxol-5-ylmethyl)-2-(m- and p-nitrophenyl)-1,3-thiazolidin-4-ones: different roles of the oxygen atoms
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https://doi.org/10.1515/zkri-2015-1893
Keywords for this article
crystal structures; hydrazones; quinoline derivatives; π···π stacking interactions

Articles in the same Issue

  1. Frontmatter
  2. Graphical Synopsis
  3. Inorganic Crystal Structures
  4. Single-crystal X-ray diffraction study of Cs2Er[Si6O14]F and Cs2Er[Si4O10]F
  5. Rb2Ca2Si3O9: the first rubidium calcium silicate
  6. Organic and Metalorganic Crystal Structures
  7. Variations in the intermolecular interactions in (E) benzaldehyde 7-chloro-1-methyl- 4H-quinolinyl-4-ylidene-hydrazone and seven halo derivatives
  8. Crystal structures of 3-(2H-1,3-benzodioxol-5-ylmethyl)-2-(m- and p-nitrophenyl)-1,3-thiazolidin-4-ones: different roles of the oxygen atoms
  9. Crystal structure and Hirshfeld analysis of the kryptoracemate: bis(mefloquinium) chloride p-fluorobenzenesulphonate
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